
Concept explainers
Shikimic acid is a key biosynthetic intermediate in plants and microorganisms. In nature, shikimic acid is converted to chorismate, which is then converted to prephenate, ultimately leading to
(a) Comment on the several transformations that occur between d-mannose and 2. What new functional groups are formed?
(b) What is accomplished in the steps from 2 to 3, 3 to 4, and 4 to 5?
(c) Deduce the structure of compound 9 (a reagent used to convert 5 to 6), knowing that it was a carbanion that displaced the trifluoromethanesulfonate (triflate) group of 5. Note that it was compound 9 that brought with it the required
SCHEME 1 The synthesis of
(a) acetone, HA;
(b) BnCl, NaH;
(c) HCl, aq. MeOH;
(d)
(e)
(f)
(g) 9, NaH;
(h)
(i) NaH;
(j) 60% aq.

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Chapter 22 Solutions
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